Lauric Acid → Beta-Naphthyl laurate

HRID 1351043Notes

Reaction equation

HRID 1351043 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].CCOCC.[C:17](O)(=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CS(O)(=O)=O>>[C:17]([O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 3

HCID 3893Lauric AcidHCID 6395Methanesulfonic AcidHCID 197425842-Naphthol Ether

Product 1

HCID 80656Beta-Naphthyl laurate

Conditions

Temperature
220 °C

Procedure

To a four neck round bottom flask fitted with nitrogen inlet, mechanical stirrer, temperature probe and condenser is charged 1197.03 g (2.11 moles) of the Alkoxylate from example 18 and 402.97 g (2.01 moles) of Lauric Acid. A catalytic amount of Methanesulfonic Acid (1.6 g) is charged and the reaction mixture is heated to 220° C. under nitrogen sparge. The reaction is monitored by measuring the acid value to an AV of preferably less than 5. Once the AV is reached, the temperature is cooled to 85° C. and the catalyst is neutralized with an equivalent molar amount of 45% KOH and washed once with water. The reaction is dried under vacuum yielding the desired product.

Workup

  1. customTo a four neck round bottom flask fitted with nitrogen inlet, mechanical stirrer
  2. customsparge
  3. temperaturethe temperature is cooled to 85° C.
  4. washwashed once with water
  5. customThe reaction is dried under vacuum

Sources & evidence

ORD record
ord-c00d9e0212df48eeabdcb65c54b26297
Source dataset
uspto-grants-2007_05
Patent number
US07217424B2

Reaction notes

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